103786-19-2Relevant academic research and scientific papers
Orthogonally protected 1,2-diols from electron-rich alkenes using metal-free olefin syn-dihydroxylation
Colomer, Ignacio,Barcelos, Rosimeire Coura,Christensen, Kirsten E.,Donohoe, Timothy J.
, p. 5880 - 5883 (2016)
A new method for the stereoselective metal-free syn-dihydroxylation of electron-rich olefins is reported, involving reaction with TEMPO/IBX in trifluoroethanol (TFE) or hexafluoroisopropanol (HFIP) and the addition of a suitable nucleophile. Orthogonally
Copper- and Nickel-Catalyzed Cross-Coupling Reaction of Monofluoroalkenes with Tertiary, Secondary, and Primary Alkyl and Aryl Grignard Reagents
Shi, Hongyan,Dai, Wenpeng,Wang, Biyun,Cao, Song
, p. 459 - 463 (2018)
A highly efficient cross-coupling reaction of monofluoroalkenes with tertiary, secondary, and primary alkyl and aryl Grignard reagents in the presence of a catalytic amount of copper or nickel catalyst, respectively, has been developed. The reactions proceeded smoothly at room temperature, providing (E)-alkene isomers in moderate to high yields. Plausible mechanisms of the Ni-catalyzed coupling reaction of monofluoroalkene with Grignard reagents are suggested.
A transition-metal-free Heck-type reaction between alkenes and alkyl iodides enabled by light in water
Liu, Wenbo,Li, Lu,Chen, Zhengwang,Li, Chao-Jun
supporting information, p. 6170 - 6174 (2015/06/08)
A transition-metal-free coupling protocol between various alkenes and non-activated alkyl iodides has been developed by using photoenergy in water for the first time. Under UV irradiation and basic aqueous conditions, various alkenes efficiently couple with a wide range of non-activated alkyl iodides. A tentative mechanism, which involves an atom transfer radical addition process, for the coupling is proposed.
Photocatalytic synthesis of dihydrobenzofurans by oxidative [3+2] cycloaddition of phenols
Blum, Travis R.,Zhu, Ye,Nordeen, Sarah A.,Yoon, Tehshik P.
supporting information, p. 11056 - 11059 (2015/03/30)
We report a protocol for oxidative [3+2] cycloadditions of phenols and alkenes applicable to the modular synthesis of a large family of dihydrobenzofuran natural products. Visible-light-activated transition metal photocatalysis enables the use of ammonium persulfate as an easily handled benign terminal oxidant. The broad range of organic substrates that are readily oxidized by photoredox catalysis suggests that this strategy may be applicable to a variety of useful oxidative transformations.
Analyzing site selectivity in Rh2(esp)2-catalyzed intermolecular C-H amination reactions
Bess, Elizabeth N.,Deluca, Ryan J.,Tindall, Daniel J.,Oderinde, Martins S.,Roizen, Jennifer L.,Du Bois,Sigman, Matthew S.
supporting information, p. 5783 - 5789 (2014/05/06)
Predicting site selectivity in C-H bond oxidation reactions involving heteroatom transfer is challenged by the small energetic differences between disparate bond types and the subtle interplay of steric and electronic effects that influence reactivity. Herein, the factors governing selective Rh 2(esp)2-catalyzed C-H amination of isoamylbenzene derivatives are investigated, where modification to both the nitrogen source, a sulfamate ester, and substrate are shown to impact isomeric product ratios. Linear regression mathematical modeling is used to define a relationship that equates both IR stretching parameters and Hammett σ+ values to the differential free energy of benzylic versus tertiary C-H amination. This model has informed the development of a novel sulfamate ester, which affords the highest benzylic-to-tertiary site selectivity (9.5:1) observed for this system.
One-pot synthesis of substituted styrenes from vicinal dibromoalkanes and arylboronic acids
Tikhonov,Vasil'ev,Chirskaya,Struchkova,Merkulova,Zlotin
, p. 122 - 129 (2008/02/08)
Dehydrobromination of vicinal dibromoalkanes in systems comprising 1,2-dimethoxy-ethane, N-butyl-N′-methylimidazolium tetrafluoroborate (or tetrabutylammonium bromide), and a base with subsequent palladium-catalyzed cross-coupling of the thus formed bromoalkenes with arylboronic acids furnished substituted styrenes. Springer Science+Business Media, Inc. 2007.
The Stereocontrolled Horner-Wittig Reaction: Synthesis of Disubstituted Alkenes
Buss, Antony D.,Warren, Stuart
, p. 2307 - 2326 (2007/10/02)
Addition of the lithium derivatives of phosphine oxides Ph2P(O)CH2R1 to aldehydes gives erythro adducts (11) with good stereoselectivity.Reduction of α-diphenylphosphinoyl ketones (12) gives threo adducts (11) with even better stereoselectivity.Purification by flash chromatography and/or crystallisation followed by elimination of Ph2PO2 gives pure Z- or E-alkenes with high material conversion.Explanations are offered for the stereoselectivities, conditions defined for full stereochemical control, and guidelines suggested for approaches to a given alkene.
Reactivity of Aryl Vinyl Di-?-methane Systems. Mechanistic and Exploratory Organic Photochemistry
Zimmerman, Howard E.,Swafford, Richard L.
, p. 3069 - 3083 (2007/10/02)
The di-?-methane rearrangement of a series of meta and para substituted arylvinylmethane reactants was investigated with the aim of determiningthe patterns of reactivity in systems in which initial excitation is localized in the aryl moiety.Thus the photo
